Acetic Acid → Pentyl 2-(3-chloro-2-pyridinyl)-5-oxopyrazolidine-3-carboxylate

HRID 1513376노트

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HRID 1513376 반응식
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Na].[Cl:8][C:9]1[C:10]([NH:15][NH2:16])=[N:11][CH:12]=[CH:13][CH:14]=1.[C:17](OC)(=[O:24])/[CH:18]=[CH:19]\[C:20](OC)=[O:21].C(O)(=O)C>O>[Cl:8][C:9]1[C:10]([N:15]2[CH:19]([C:20]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:21])[CH2:18][C:17](=[O:24])[NH:16]2)=[N:11][CH:12]=[CH:13][CH:14]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 62761-PentanolHCID 5561003-Chloro-2-hydrazinylpyridineHCID 5271565Dimethyl maleateHCID 5360545Sodium2회

생성물 1

HCID 59549450Pentyl 2-(3-chloro-2-pyridinyl)-5-oxopyrazolidine-3-carboxylate수율 42%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a three-necked flask, pentan-1-ol (150 mL) was added. And the sodium (3.0 g, 0.13 mol) was added partially. The reaction mixture was heated to reflux for 30 minutes at 100° C. When the sodium reacted completely, the mixture was cooled to 60° C. Then 3-chloro-2-hydrazinylpyridine (12.75 g, 98%, 0.09 mol) were added and reacted for 30 minutes. The dimethyl maleate (12.50 g, 0.11 mol) was added dropwise. The reaction mixture was heated to reflux for 10 minutes. After cooled to 65° C., the reaction mixture was neutralized with glacial acetic acid (13.04 g, 0.23 mol) and diluted with water (300 mL). After cooled to room temperature, solid is separated out to be filtered and, washed with 40% aqueous solution of ethanol (3×50 mL) and dried to give pentyl 2-(3-chloro-2-pyridinyl)-5-oxopyrazolidine-3-carboxylate (12.00 g) as a orange solid in 42% yield. HPLC area normalization method content is 95% (Analytical condition: chromatographic column: ZORBAX Eclipse XDB-C8 4.6×150 mm 5 μm, mobile phase:the ratio of acetonitrile to water is 70:30).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperaturethe mixture was cooled to 60° C
  3. customreacted for 30 minutes
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux for 10 minutes
  6. temperatureAfter cooled to 65° C.
  7. temperatureAfter cooled to room temperature
  8. customsolid is separated out
  9. filtrationto be filtered
  10. washwashed with 40% aqueous solution of ethanol (3×50 mL)
  11. customdried

출처 및 근거

ORD 기록
ord-f73c69cd99274b18a58ee56e06f775ef
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217179B2

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